Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes

Wan Seok Yoon; Won Jun Jang; Woojin Yoon; Hoseop Yun; Jaesook Yun

doi:10.1038/s41467-022-30286-8

Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes

Wan Seok Yoon, Won Jun Jang, Woojin Yoon, Hoseop Yun, Jaesook Yun

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

Asymmetric construction of C(sp³)–C(sp³) bond with good stereocontrol of the two connecting carbon centres retaining all carbon or hydrogen substituents is a challenging target in transition metal catalysis. Transition metal-catalysed reductive coupling of unsaturated π-substrates is considered as a potent tool to expediently develop the molecular complexity with high atom efficiency. However, such an asymmetric and intermolecular process has yet to be developed fully. Herein, we report an efficient strategy to reductively couple two prochiral conjugate alkenes using a copper-catalysed tandem protocol in the presence of diboron. Notably, this transformation incorporates a wide range of terminal and internal enynes as coupling partners and facilitates highly diastereo- and enantioselective synthesis of organoboron derivatives with multiple adjacent stereocentres in a single operation.

Original language	English
Article number	2570
Journal	Nature Communications
Volume	13
Issue number	1
DOIs	https://doi.org/10.1038/s41467-022-30286-8
State	Published - Dec 2022

Bibliographical note

Funding Information:
This work was supported by Samsung Science and Technology Foundation under Project Number SSTF-BA2002-08 (to J.Y.) X-ray structural analysis was supported by Basic Science Research Program through the National Research Foundation of Korea (2019R1I1A2A01058066, to H.Y.).

Publisher Copyright:
© 2022, The Author(s).

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title = "Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes",

abstract = "Asymmetric construction of C(sp3)–C(sp3) bond with good stereocontrol of the two connecting carbon centres retaining all carbon or hydrogen substituents is a challenging target in transition metal catalysis. Transition metal-catalysed reductive coupling of unsaturated π-substrates is considered as a potent tool to expediently develop the molecular complexity with high atom efficiency. However, such an asymmetric and intermolecular process has yet to be developed fully. Herein, we report an efficient strategy to reductively couple two prochiral conjugate alkenes using a copper-catalysed tandem protocol in the presence of diboron. Notably, this transformation incorporates a wide range of terminal and internal enynes as coupling partners and facilitates highly diastereo- and enantioselective synthesis of organoboron derivatives with multiple adjacent stereocentres in a single operation.",

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AU - Yun, Jaesook

N1 - Funding Information: This work was supported by Samsung Science and Technology Foundation under Project Number SSTF-BA2002-08 (to J.Y.) X-ray structural analysis was supported by Basic Science Research Program through the National Research Foundation of Korea (2019R1I1A2A01058066, to H.Y.). Publisher Copyright: © 2022, The Author(s).

PY - 2022/12

Y1 - 2022/12

N2 - Asymmetric construction of C(sp3)–C(sp3) bond with good stereocontrol of the two connecting carbon centres retaining all carbon or hydrogen substituents is a challenging target in transition metal catalysis. Transition metal-catalysed reductive coupling of unsaturated π-substrates is considered as a potent tool to expediently develop the molecular complexity with high atom efficiency. However, such an asymmetric and intermolecular process has yet to be developed fully. Herein, we report an efficient strategy to reductively couple two prochiral conjugate alkenes using a copper-catalysed tandem protocol in the presence of diboron. Notably, this transformation incorporates a wide range of terminal and internal enynes as coupling partners and facilitates highly diastereo- and enantioselective synthesis of organoboron derivatives with multiple adjacent stereocentres in a single operation.

AB - Asymmetric construction of C(sp3)–C(sp3) bond with good stereocontrol of the two connecting carbon centres retaining all carbon or hydrogen substituents is a challenging target in transition metal catalysis. Transition metal-catalysed reductive coupling of unsaturated π-substrates is considered as a potent tool to expediently develop the molecular complexity with high atom efficiency. However, such an asymmetric and intermolecular process has yet to be developed fully. Herein, we report an efficient strategy to reductively couple two prochiral conjugate alkenes using a copper-catalysed tandem protocol in the presence of diboron. Notably, this transformation incorporates a wide range of terminal and internal enynes as coupling partners and facilitates highly diastereo- and enantioselective synthesis of organoboron derivatives with multiple adjacent stereocentres in a single operation.

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Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes

Abstract

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